Method for preparing trans polyhydroxystilbene compounds

A technology of polyhydroxystilbene and dihydroxyphenylacetic acid, which is applied in the field of preparation of trans-polyhydroxystilbene compounds, can solve the problems of difficult separation, few synthesis studies, cumbersome steps, etc., and achieve good atom economy, Effects with simple post-processing and short reaction times

Inactive Publication Date: 2010-07-14
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, there are relatively few studies on the synthesis of such compounds, and literature reports generally use Wittig reaction (J Med Chem, 2003, 46: 3546-3554; Tetrahedron Lett, 1970, 47: 4051-4053), Wittig-Hornor reaction (Chin Chem Lett, 2000, 11(3): 217-218; China Food Additives, 2007, 3: 54-56) and Knoevenagel condensation ([P]CN: 200310111885.4, 2003-10-27.) to construct the stilbene skeleton
When synthesizing the target compound, these methods either require hydroxyl protection and deprotection, or group transformation, and are easy to obtain cis-trans mixtures, which are difficult to separate, require further transformation, and the steps are cumbersome

Method used

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  • Method for preparing trans polyhydroxystilbene compounds
  • Method for preparing trans polyhydroxystilbene compounds
  • Method for preparing trans polyhydroxystilbene compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) Take 29.4g (0.1mol) of 3,5-dibromophenylacetic acid, 40g (1mol) of NaOH, CuSO 4 .5H 2 O25.0g (0.1mol), add H 2 080ml in a 250ml stainless steel reactor equipped with a thermometer and a reflux condenser, under nitrogen protection, stirred and heated at 110°C for 72 hours, cooled the reaction solution with suction and filtered, acidified the filtrate with hydrochloric acid to adjust the pH to 4-5, extracted with ethyl acetate, and separated the organic layer, dried, and concentrated under reduced pressure to obtain crude product 3,5-dihydroxyphenylacetic acid 15.1g, yield 90%; MS m / z: 168 (M + ).

[0040] (2) Weigh 1.68g (10mmol) of 3,5-dihydroxyphenylacetic acid, 1.46g (12mmol) of 4-hydroxybenzaldehyde and add in the there-necked flask equipped with a thermometer and a reflux condenser, then add 3.03g of triethylamine ( 30mmol), 6.12g (60mmol) of acetic anhydride, refluxed at 120°C for 6 hours, after the reaction was complete, cooled the reaction solution and pou...

Embodiment 2

[0045] (1) Take 29.4g (0.1mol) of 3,5-dibromophenylacetic acid, 48g (1.2mol) of NaOH, CuSO 4 16.0g (0.1mol), add H 2 O100ml is placed in a 250ml stainless steel reactor equipped with a thermometer and a reflux condenser. Under nitrogen protection, stir and heat at 110°C for 70 hours. layer, dried, and concentrated under reduced pressure to obtain 15.6 g of crude product 3,5-dihydroxyphenylacetic acid, with a yield of 93%.

[0046] (2) Weigh 1.68g (10mmol) of 3,5-dihydroxyphenylacetic acid, 1.52g (10mmol) of 3-methoxy-4-hydroxybenzaldehyde and add it into a three-necked flask equipped with a thermometer and a reflux condenser, and then add 2.53g (25mmol) of triethylamine, 3.06g (30mmol) of acetic anhydride, refluxed at 110°C for 8 hours. After the reaction was complete, the reaction solution was cooled and poured into water to stir, and a large amount of solids were precipitated. The cake was dried and then recrystallized to obtain 3.42 g of E-2-(3,5-diacetoxyphenyl)-3-(3'-m...

Embodiment 3

[0051] (1) Take 29.4g (0.1mol) of 3,5-dibromophenylacetic acid, KOH56g (1mol), CuSO 4 .5H 2 O25.0g (0.1mol), add H 2 O150ml is placed in a 250ml stainless steel reactor equipped with a thermometer and a reflux condenser. Under nitrogen protection, stir and heat at 120°C for 60 hours. layer, dried, and concentrated under reduced pressure to obtain crude product 3,5-dihydroxyphenylacetic acid 15.8g, yield 94%;

[0052] (2) Weigh 1.68g (10mmol) of 3,5-dihydroxyphenylacetic acid and 1.38g (10mmol) of 3,4-dihydroxybenzaldehyde into a three-necked flask equipped with a thermometer and a reflux condenser, and then add triethylamine 4.04g (40mmol), 6.12g (60mmol) of acetic anhydride, reflux at 115°C for 7 hours. After the reaction is complete, cool the reaction solution and pour it into water to stir. A large amount of solids are precipitated. After standing for a while, suction filter and dry the filter cake After recrystallization, 3.60 g of E-2-(3,5-diacetoxyphenyl)-3-(3',4'-dia...

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Abstract

The invention discloses a method for preparing trans polyhydroxystilbene compounds. The method comprises the following steps: 3,5-dibromophenylacetic acid is converted into 3,5-dihydroxyphenyl acetic acid under alkali conditions;3,5-dihydroxyphenyl acetic acid and 4-hydroxybenzaldehyde compounds are subject to a Perkin reaction to obtain E-2-(3,5-diacetyl phenyl)-3-(4'-acetoxyl phenyl)acrylic acid compounds; and the E-2-(3,5-diacetyl phenyl)-3-(4'- acetoxyl phenyl)acrylic acid compounds are subject to decarboxylation isomerization and hydrolysis reaction, or hydrolysis and decarboxylation isomerization reaction to obtain the trans polyhydroxystilbene compounds. The all-trans products obtained by using the method have the advantages of favorable atom economy, simple synthetic route, simpleaftertreatment, low cost, high yield and the like, and can easily realize large-scale preparation.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of trans polyhydroxy stilbenes. Background technique [0002] Trans-polyhydroxy stilbenes (structure shown in Formula 1) are a class of compounds with important pharmacological activities. [0003] [0004] where R 1 , R 2 = H, OH or OCH 3 . [0005] Representative compounds in trans polyhydroxy stilbenes are resveratrol (Resveratrol, E-3, 4', 5-trihydroxy stilbene), Piceatannol (E-3, 3', 4', 5-tetrahydroxystilbene) and iso-Rhapontigenin (iso-Rhapontigenin, E-3,4',5-trihydroxy-3'-methoxystilbene), etc. Resveratrol widely exists in many foods (such as mulberries, peanuts and grapes, etc.), and has anti-cancer, anti-cancer, hypolipidemic, anti-thrombotic, antioxidant and anti-inflammatory effects (Inter J Biochem & Cell Biol, 2005, 37: 1709 -172; J Med Chem, 2003, 46: 3546-3554); Resveratrol can also activate Sirtuins enzymes, thereby delaying the agin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/23C07C41/26C07C41/18C07C37/50C07C39/21C07C37/055
Inventor 邹永肖春芬陈煜魏文孙洪宜吕泽良
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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